Acetone → HCID 22648204, compound

Participants

Reaction Steps

To a solution of 14 mg of 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-piperidin-4-yl-1,6-naphthyridin-2(1H)-one in 1 mL of MeOH was added 0.1 mL of acetone, then 9 mg of sodium cyanoborohydride. The mixture was stirred 5 h at rt, then diluted with 1 mL of EtOAc and 10 mL NaHCO3. The phases were separated and the aqueous phase was extracted with 2×10 mL of EtOAc. The combined organics were washed with 10 mL of brine, dried (Na2SO4), and concentrated. The residue was purified by preparative thin-layer chromatography, eluting with 95:5 CH2Cl2-2M NH3 in MeOH to yield the title compound. Mass spectrum (ESI) 528 (M+1). 1H NMR (500 MHz, CDCl3): selected peaks δ 1.07 (d, J=6.5 Hz, 6H), 1.71 (br s, 2H); 1.99 (br s, 2H); 2.26 (br s, 2H); 2.80 (br s, 2H); 3.02 (br s, 2H).

Provenance & Evidence